Ethylamine → (2E)-3-(3-Bromophenyl)-N-ethyl-2-propenamide

HRID 441558Notes

Reaction equation

HRID 441558 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](Cl)=[O:8].[CH2:13]([NH2:15])[CH3:14]>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:15][CH2:13][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 14959106trans 3-Bromocinnamoyl chloride

Product 1

HCID 688145(2E)-3-(3-Bromophenyl)-N-ethyl-2-propenamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of trans 3-bromocinnamoyl chloride (12.3 g) in anhydrous toulene (150 ml) was added slowly with stirring to a solution of ethylamine (10 g) in dry ether (100 ml) at room temperature. The reaction mixture was heated at reflux for 1 hour, and the solvent and excess amine were then removed under reduced pressure. The residue was triturated with water, filtered, and recrystallized from ethanol-water to give trans 3-bromo-N-ethylcinnamamide, m.p. 89°-90° C., as a white crystalline material. NMR and IR spectra as well as elemental analysis were consistent with the assigned structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customthe solvent and excess amine were then removed under reduced pressure
  4. customThe residue was triturated with water
  5. filtrationfiltered
  6. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-0b21772bad724033905ed838f46683e4
Source dataset
uspto-grants-1977_08
Patent number
US04041071

Reaction notes

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